


A Long Time

by proseccoandpd



Category: Chicago PD (TV)
Genre: F/M, First Kiss, First Time, Humor, Love
Language: English
Status: Completed
Published: 2021-01-23
Updated: 2021-02-01
Packaged: 2021-03-14 18:35:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 5,113
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28925184
Author URL: https://archiveofourown.org/users/proseccoandpd/pseuds/proseccoandpd
Summary: What may have happened after the screen cut to black after 8x03.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 5
Kudos: 110





	1. Chapter 1

_“It’s been a long time…since I’ve seen you as just my partner.”_

Hailey wiped away the tears falling from her eyes, and shakily looked up at Jay, who was looking at her with the most intense gaze. Before she could process what was happening, think about the words she just uttered, Jay’s lips were on hers.

Jay stepped forward with a force, wrapping one arm around her back while the other slipped under her coat and settled around her waist. Acting on pure instinct, Hailey rose to meet him on her tip toes. She stumbled into his body, but Jay only tightened his grip on her. As she smiled into the kiss, wrapping her arms around his neck, as if they had done this a million times before, she let her hand slide down his chest, settling over his heart, feeling it beat against her palm.

They pulled away when their need for air became apparent, and Jay smiled down at her, keeping his left hand on her hip. His right hand left her back and found hers, giving it a squeeze. Overwhelmed by how her whole world shifted in the last ten minutes, Hailey buried her forehead into his chest, taking a deep breath and willing the tears to stop.

Feeling her back rise with her deep breath, Jay wrapped her in a hug, again pulling her body tightly into his. “Let’s get outta here.” He pressed his cheek against her hair and inhaled the sweet smell of her conditioner, kissing her forehead as he pulled back. Hailey nodded against him and wiped the tears from her face as he gently tugged on her hand, leading her to the door and out to the cold air.

They fell into step together as they walked to Jay’s truck, which was parked at the other end of the street. As the pair approached the passenger side door, Jay stopped walking and wrapped an arm around Hailey’s shoulders, again pulling her into his body. He dropped his head to be level with Hailey and caught her lips in another kiss, this time gentler but still a little needy.

“So we’re clear, it’s been a long time for me too Hailey.” She raised her head and smiled at him, feeling herself slipping back into their teasing, flirty banter, “I think that first kiss confirmed that.” Hailey raised herself up on her tip toes to be eye level with him, her blue eyes darkening as her body ached for contact with his, “Your place or mine?”

Jay felt his need for her course through his body as her normally ocean colored eyes turned a darker shade, “Yours.” He slipped both of his hands under her coat to rest on her waist, his thumbs sneaking under her top, his touch making her shiver. He stepped into her body, gently pushing her back until she rested against the side of his truck and he dipped his head down to meet her lips, kissing her again, this time letting her know just how badly he needed and wanted her. Hailey brought her hands to his chest, running them up and down the hard planes of muscle, as she let her fingers dance right above his waist line, she felt his body respond to her touch almost instantly.

She brushed her lips along his jaw line until she made it to his ear lobe and whispered, “Take me home, Jay.” Not removing his lips from the path he was taking down her neck, he blindly reached his hand out to grip the door handle. He opened the door, the cab of the truck blasting heat at them, and bent down slightly to get a better grip on Hailey’s waist, lifting her up and onto the passenger seat. She let out a shocked little gasp against the side of his face, partly because she felt herself airborne and partly because of the things his teeth and tongue were doing to her.

He paused his assault on her skin and kissed his way back up her neck to be at eye level with her, their eyes locking and sharing maybe their most intense stare yet. Hailey reached over to secure her seatbelt and she felt her insides exploding as Jay followed the belt with his eyes, watching it drag over her body. He swallowed and pressed a light kiss to her lips before closing her door and jogging around to the driver’s side.

The drive to Hailey’s place felt like hours, when really it was only ten minutes. Her hand had settled on his knee, her fingertips tracing nonsense patterns along his leg. He laid his hand on top of hers and laced their fingers, reveling in how perfectly her hand fit within his. He parked in her driveway and followed her up the stairs and through her front door. She slipped her coat off and tossed it on the bench in her entryway, and turned to look at Jay. She stepped closer to his body and reached her hands under his jacket, sliding it off his shoulders and tossing it to the side to join her own.

Jay placed one hand behind her neck and the other again settled on her waist, his thumb gently stroking her jawline, “You are gorgeous.” He snaked his hand up the back of her head and gently tugged the band out of her hair, letting her long locks flow down her back. Hailey lifted herself up on her tiptoes, now that her boots were off, their height difference became even more apparent. Jay met her halfway and their lips met, Hailey pouring all her pent-up emotion and desire and need for him, slipping her tongue between his lips. Jay let out a groan against her mouth and she pulled him even closer, placing both her hands on either side of his face, mumbling against his lips, “Have you looked in the mirror lately?” Her hands dropped from his face and trailed down to the hem of his shirt, finally slipping her hands underneath and pulling it over his head.

His need to feel her bare skin pressed against his own took over, and he followed her lead, unbuttoning her plaid top one by one. Jay bent in front of her body, placing light kisses down her abdomen as he exposed more and more of her. Hailey placed both hands on his shoulders as he descended her body, steadying herself as she felt her heart beating out of her chest, biting her lower lip to contain herself. Jay kissed his way back up, pausing over a scar on her ribcage, making a mental note to ask her about that later. He placed a kiss on the skin between her breasts, fingers on his right hand ghosting over her nipple through her bra, and Hailey squeezed his shoulder blade at his touch. He knew Hailey better than he knew himself, but now, there was so much more to learn, and he couldn’t wait to figure out what made her squeeze his arms, arch into his body, cry out his name.

Jay lifted her up effortlessly, Hailey’s legs wrapping around his waist on instinct and her head dipping to place hot, open mouthed kisses down his neck. He made his way up her stairs and into her bedroom, sitting on the edge of her bed so she was straddling his lap. Hailey continued her path down his neck, her lips travelling over his collar bone, pausing at the faded mark there, covering it with her lips and lightly sucking while she rolled her hips against his, feeling his bulge press against her jeans in the most teasing of ways. Jay let out a husky groan, making goosebumps rise on her skin. She couldn’t wait to hear that sound again, breathed out along her body somewhere.

Jay’s hands travelled up her back, pausing at her bra strap, as he pulled back from her slightly, “If we keep going, I won’t be able to stop.” Hailey sat back on her thighs, giving him a smirk and reached her hand up to pull one strap off her shoulder, “Who said I ever want you to stop?” As her hand was making its way across her chest to the other shoulder, Jay gently gripped her wrist and tugged her hand away. His fingers unbuckled the clasp at the middle of her back and the material fell away from her body, Jay gently pulling it down her arm and tossing it to the side. He wrapped an arm around her back and pulled her to his chest, feeling her taut nipples pressing against him. His other hand cupped her bare breast, running his thumb across her nipple before rolling it between his thumb and forefinger, causing Hailey to let out a whimper she couldn’t control.

Hailey involuntarily rolled her hips against Jay’s again, this time both of them letting out a needy sound. Jay gripped her hips again, flipped her onto her back, and he crawled over her, his head dipping back down to take her other breast into his mouth. With Hailey’s breathy sighs urging him on, his teeth were leaving marks only he would be able to see. Hailey’s hands travelled down his chest and down to his waistline, undoing his belt buckle, opening the button on his jeans and sliding them off his body as far down as she could reach. She looked down between their bodies, his boxers doing little to hide how much want he felt for her.

Jay pulled himself away from her chest, his arms bracketing her, as he shimmied out of his jeans and brought his knees to straddle her legs. All he could do was watch as she gripped him through his boxers, her eyes widening as she felt how thick he was in her hands. Hailey lightly ran her fingers up and down his length, watching as his eyes fluttered shut at her touch. Needing to actually feel him, Hailey dipped her hand below the waist band of his boxers and took his full length in her hands, rubbing her thumb along the tip, already feeling the wetness gathering there. She propped herself up on her left arm so she could reach his neck, attaching her lips there, biting and sucking, while her hand still moved up and down his length. Jay felt his resolve breaking, and if he didn’t control himself, he’d probably finish right here in her hand.

Feeling her grip tighten on him and her speed quicken along him, he dropped his head onto her shoulder and mustered all of his self control, reaching between their bodies and stilling her hand, “Hailey..” She laid her head back down on her comforter and smiled at him, “Jay.” She wiggled her hand free from his grip, again tightening her hand around him and rubbing up and down, “We have all night, the rest of our nights, just let yourself go.” Jay, aware of what she just said, kissed a spot on her shoulder where his head was laying, “You’re the last first time I want Hailey.” He lifted his head up to see her face, and he was met with her beaming smile, “Me too, Jay.” Again, he pulled her hand away, kissed her palm and sat back on his knees, working to undo her jeans. She raised her hips to help him peel them off her legs, and he kissed her navel, below her bellybutton, above where she needed him most.

Hailey let out a soft sigh as she felt his lips there. And then she felt his lips moving lower and his fingers pulling down her simple cotton thong. If she knew her night would be ending with this specimen of a man undressing her, she would’ve chosen her undergarments more wisely. All coherent thoughts left her mind as she felt his lips on her, his shoulders nudging her knees further apart for him, his tongue sliding inside of her. She couldn’t help but cry out his name as her hands fell to his head, running them through his hair. He snaked one hand around her hip to hold her steady against him as he kept exploring, pleasuring with his tongue and lips.

Hailey propped herself up on her elbows, needing to see him. At the same time, Jay also glanced up, their eyes locking. He gave her one more intimate kiss before pulling away and bringing his face to meet hers. She placed her hand behind his head and brought his lips to hers, tasting herself at the same time and moaned into him. She was so mesmerized by this, that as he slipped one finger inside of her, her whole body arched into him. Jay pushed her body down with his torso, his left hand burying itself in her hair as he laid her down, and he added one more finger into her heat. Her knees opened for him, letting him rest her hips against hers, as his fingers explored her most intimate place. He reached her spot, and her chest arched into his, again crying out his name, telling him he was right there, begging him not to stop. Their eyes stayed locked on the other as he saw her reach her limit, watched as she closed her eyes, feeling her legs shake around his, hearing her whimper as his fingers continued to stroke her through it.

When she opened her eyes, she felt his hand still on her, and she reached up to kiss him, “That was..wow.” Jay smirked at her, knowing he thoroughly pleased her, knowing he was nowhere near finished with her. “I aim to please, Hails.” He slipped his hand out from inside of her, and before he could stop her, Hailey rolled them over so she was straddling his waist, so he could feel her wetness on his low abdomen. She kissed down his abdomen, circling her tongue around his navel, and she felt him harden even more against her thigh. “You certainly did.” She shifted herself lower, and pulled his boxers down his long, lean legs. She took him in her hand again, stroking him a few times, before she bent down and circled her lips around his tip. She heard his sharp inhale and felt his hips rise up slightly.

Hailey continued, her lips sucking, her teeth dragging and her hands massaging, all while listening to him breathe into the pleasure and call her name softly. He reached down to lace his fingers through hers, squeezing them, letting her know that he was close to his limit. Hailey squeezed back, but kept going, taking him deeper into her mouth, feeling him twitch against her. He also propped himself on his elbow, needing to see her. Her cheeks were hollow around him and her long, blonde hair curtained his hips. Feeling eyes on her, Hailey glanced up through her eyelashes, meeting his gaze and she took him even further, her cheeks becoming hollower. That was Jay’s undoing. He called out her name as his hips bucked into her, his body releasing itself into her mouth as Hailey gently stroked his base, not caring that he finished in her mouth.

She swirled her tongue around his tip once more before releasing him, and all Jay wanted now was to be buried inside her, to feel their bodies joined, to not know where he started and she began. He wanted to feel her arms around his back as he pushed into her, giving her all the pleasure and love she deserved. She smiled at him as she crawled up his body, he stopped her halfway and pushed her on her back, Hailey not missing a beat, wrapping her arms around his neck. He bent down to brush his lips against hers, “I need you so bad,” Hailey kissed him back, “You have me Jay, I’m all yours.”

Just as Jay was about to take himself in his hand and line himself up to her, he heard a ringing coming from behind him, “No, no, no, no way.” He paused, hearing it stop. He picked up where he was, but Hailey reached her hand out to stop him, waiting to hear if her phone would ring too. As if on cue, it started buzzing on the nightstand where she plugged it in to charge. She deflatingly laid her head back, “Why.” She reached over, seeing a missed call from Kim. “It’s Burgess.” She rolled her eyes and sat up, kissing him again, “I think we’re going to have to pick this up later.” Jay rolled his eyes and groaned, pulling her into him and kissing her softly, “I think you’re right.” He picked up his phone and saw a missed call from Kevin, “Atwater called.”

Jay called Kevin back, as Hailey pulled on the same jeans she was wearing earlier, but walked to her closet to grab a new top, so as not to alert the rest of the group to this new found development between them. She slipped on the rust colored hoodie, and turned around, seeing Jay struggling to get his jeans on one handed. Hailey stepped towards him, pulling the jeans over his hips, and she reached into his boxers once more, Jay’s eyes bugging out of his head as he tried to focus on what was being relayed on the phone. She tucked him in so his zipper would close, and she redid his belt buckle as he ended the call, “Copy that. I’ll swing by Upton’s place, we’ll be there in 30 minutes.”

She chuckled, “Gunna swing by, huh?” He followed her out of her room and down the stairs, bending down to grab his shirt that was discarded some time ago. “That’s not all I’m going to do.” He threw her a wink. She slipped on her jacket and pulled a black beanie over her head, trying to hide the mess his hands made. “I’m gunna hold you to that.” She locked her door, and laced her fingers through his hand that was held out for her, the pair walking to his truck, neither knowing how they were ever going to focus on the scene they were headed to. 


	2. Chapter 2

**Notes for the Chapter:**

> Hi friends! We were #blessed this week with all the Upstead content. *insert heart eyes* Had to write a part 2 to this after the opening scene. I wanted to fill in the blanks between the bar and the morning, hope this did the trick!
> 
> Thank you so much for reading/reviewing/saving/favoriting! Makes me so happy. Happy Reading!
> 
> xo, S.

Just as Jay reached the driver’s side door, his phone rang again, Kevin’s name once again flashing across his screen.

“What in the hell. We’re coming.” He mumbled under his breath, fully annoyed that their job requires them to be ready and willing almost around the clock. Most times, he loved getting calls out to a case, feeling like he was making a difference and helping people in his city.

Tonight, was not one of those nights. Tonight, he wanted to stay in the little bubble he and Hailey created, keep her in his arms, and love her all night long.

He answered the phone, while reaching over and turning on the seat warmer, seeing Hailey shiver out of the corner of his eye. “What’s up, Kev?” Hailey buried herself in the seat, basking in the heat rising around her. Jay reached over the console and rubbed his hand up and down her leg, attempting to give her some warmth.

“Yo Jay, Sarge was first on scene, said this is a case for Gangs.” Jay nodded, “So we’re good then?” Kevin spoke further, “Yep, we’re off the hook. See you in the a.m.” A grin crept over Jay’s face, Hailey giving him a confused look. “Night Kev.”

He turned the ignition and took the key out, Hailey pouting a little as she lost her source of heat. “We’re good. It was a Gangs case.” Hailey smirked at him and raised her eyebrows, “What a fun turn of events.” She unbuckled her seat belt and hopped down from the truck, Jay following her lead and once again followed her into her building.

As quickly as the pair had gotten dressed, they got undressed even faster. As Jay closed and locked the door behind him, he grabbed Hailey’s hand and pulled her to his body. She pulled the beanie off her head and smoothed her hair down as Jay unzipped her coat and tossed it behind her, doing the same to his own jacket.

He placed both hands on the side of Hailey’s face, running his thumbs across her cheek bones. Her hands dropped to his waist, sliding her cold hands under his shirt. “Always so warm.” Jay dropped his head to her lips, pressing a soft kiss against her. “Happy to warm you up.” He felt her smirk against his lips, and felt her hands softly push him back, walking them to her bedroom.

They made it to the middle of her room and Jay deepened the kiss, sliding his tongue between her lips and dropping his hands to the hem of her sweatshirt, pulling it up over her, letting his fingers skim her sides. Hailey did the same, and tossed his henley on the floor to join her hoodie. They stood there for a second, sharing another deep stare. Hailey stepped into his space, pressing her chest against his and raised herself up on her tiptoes to meet his lips, pulling him into a kiss, letting her right hand cup the back of his head, her thumb rubbing along his hairline. Jay wrapped both of his arms around her back and pulled her fully into his body, happy to stand there and simply kiss her.

Hailey doesn’t know how long they stood there, just kissing, relishing in how their mouths moved together and basking in the feeling of being wrapped in Jay’s arms. Before she could really focus on what was happening, she felt Jay’s hand on the clasp of her bra strap, skillfully opening it with two fingers. He pulled away from her slightly to let it fall away from her body, and he couldn’t help but stare at her for a second.

Hailey kept her eyes locked on Jay’s and watched as he stepped closer to her, running his fingers up and down her sides, seeing her trying to stifle a giggle, “Ticklish?” Hailey dropped her head, “Maybe a little.” Jay chuckled himself and brought his lips to her jaw line, “So much more to learn about you.” He punctuated his words with kisses down her neck, stopping at her collarbone, Hailey leaning into his touch and biting her lip, trying to stifle the moan threatening to come out of her mouth. Jay brought his right hand up to cup her breast and roll her nipple between his fingers, pinching lightly. He saw Hailey’s eyes flutter shut at his touch and bit her lip further, “Baby, I want to hear you. Don’t keep it in.” His husky whisper sent a wave of heat through her body, straight to her core, and she desperately needed him pressed against her body.

“Jay, please.” She palmed her hand against the front of his jeans, feeling again how hard he was, her touch making his hips buck into her hand. Jay knew exactly what she was asking for, and he was happy to oblige her. He walked them backwards until they reached the edge of her bed, and his hands went to her waist, undoing her jeans and pulling them down her legs, along with her panties. Hailey followed suit and quickly undid his belt, slipping her hands under the band of his boxers and pulling them both down his long legs. She couldn’t help but take Jay in her hand, and grip him firmly, her hand running up and down his length.

Jay pushed her shoulders down gently, and laid on top of her, one of his elbows supporting his body weight. Hailey laid under him, her breathing slightly heavy. She brought her head up to meet his, pressing her lips against his in a breathy kiss. Jay slid his hand down her body and rubbed his fingers against her, before slipping them inside of her, making sure she was ready for him. Feeling his fingers, Hailey let out a whimper against his lips, “Mmm, I need to feel you Jay.”

He took himself in his hand and lined himself up with her entrance, pushing into her until his hips were flush to hers. Hailey arched her back off the bed as she felt him sliding into her, stretching her in the best way. Jay gave her a second to adjust to his size, slipping his hand behind her head, needing to keep her close. Hailey raised her hips into his, letting him know she was okay for him to continue. Hailey pulled on his arm so he was lying flush against her and brought her arms to wrap around his shoulders.

Jay thrusted into her, finding a rhythm with Hailey, and in that moment, he never felt so connected with someone, literally and physically. He swore her body was made to fit with his. Hailey wrapped her legs around his waist, wanting to feel him deeper inside of her. Jay moved harder into her, and Hailey couldn’t help but cry out his name. He buried his head into her neck as he moved, kissing any piece of skin he could get to, letting out a deep moan when he felt her walls squeeze around him. Before Hailey could react, Jay pulled away from her body and gripped her right leg, placing it on his shoulder so her body was opened further for him. He untangled his hand from her hair and placed both of his hands on either side of her face. Jay again thrusted hard into her, the new angle he had her body in sending waves of pleasure through her. Hailey’s hands circled around Jay’s wrists, squeezing as he moved inside of her, crying out his name every time he snapped his hips.

“Jay, ugh fuck, I’m so close.” Hailey moved her leg down from his shoulder and again wrapped it around his waist, his body again flush to hers. She heard his breathing quicken and his breathy moans in her ear got louder. She turned her head to press a kiss to his wrist, as his hands were still bracketed around her. She met him, thrust for thrust, until she felt her wave of intense pressure and instant release. She tossed her head back on her pillow and let the waves crash through her, squeezing Jay’s forearms. He was right behind her and soon enough, she felt his body tense, saw him close his eyes and heard him let out a deep, throaty groan as he finished, Hailey feeling his release inside her. She licked her lips at the feeling and ran her fingers through his hair, feeling his soft curls under her fingers.

Jay dropped his head to lay on her shoulder, still inside her, trying to control his breathing. Hailey laid beneath him, running her fingers along his spine soothingly. Jay lifted slightly to kiss her cheek, “You are wonderful.” Hailey smiled at him, kissing him back, “That was amazing.” He slipped out of her and rolled onto his back, bringing her with him. She naturally found a spot between his head and neck and pulled the covers over them, tangling her legs with his. Jay wrapped his arms around her, still marveling at how much has changed in the last two hours. And he couldn’t be happier.

They laid there, wrapped up in the other, for a while, until Hailey propped herself up to look at him. “Jay.” He opened his eyes and took in the expression on her face, “What’s wrong, Hails?” She smiled wide at him, “Nothing, nothing at all. I just…what do we do now?” Jay sat up and took her hand in his, rubbing her knuckles, prompting her to continue, “I meant when I said it’s been a long time since I saw you as just my partner. I…I think I started to acknowledge the shift after you were hit in the vest, after everything with your dad, and then I really understood it last fall.” Her fingers ran over the bullet scar on his shoulder and looked up at him. Jay nodded at her, “I still think about what you were going to say before the phone rang.” Hailey smiled, “Well, I think we established that.” Jay wiggled his eyebrows at her and brought his hand to her lips, “We most definitely did. But seriously Hailey, what we have here, what we’ve built…partners, friends, best friends, the blind trust…I want to make this work. You make everything better. You make me a better cop, a better friend, a better man.”

Hailey smiled and nodded along with his words. “I know that we’ve both been burned before, dating a co-worker. But you, me, this, is so much more than dating. Our bond here runs deep, and I think if we really try to make it work, it will. It has to…because my heart is yours. And it has been for a while.” Hailey let out a shaky breath she didn’t realize she was holding and looked up at him tentatively, not knowing how Jay would react to her last statement. Jay reached over and pushed a piece of hair behind her ear, “Hailey…every piece of me is yours. You’re everything to me, and then some. We will make this work.” She nodded, again feeling tears burning behind her eyes, knowing no more words were needed for now, she placed both her hands on either side of his face, and pulled him into a kiss, pouring everything she was feeling into it.

Jay pulled her body to lie on top of his own, pulling the covers around them once again, and kissed her back, running his hands up and down her body. He loved her, he’s loved her for a long time. And in due time, he’d tell her. But as he thought about it, they’d already told each other they loved the other one in countless ways…

_“Just…tell me everything. I want to help, I promise.”_

_“We’re good, and we’re always going to be good.”_

_“I’ve trusted you from the day I met you, and if I was going to follow someone blind, I’d follow you.”_

_“I’m going where you go.”_

_“I’d follow you anywhere.”_

_“Good or bad, right or wrong…”_

_“I miss the wind…and you.”_

_“I’m better with you as my partner…”_

Hailey ran her fingers through his hair, down the sides of his face, over his broad shoulders. Kissing Jay was thrilling, addicting, she couldn’t get enough. She would make this work, they could make this work.


End file.
